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seangarcia

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How do I configure Exchange Server 2003 behind ATT U-Verse 2Wire to send email?

I am stuggling with SMTP on Exchange 2003 (SBS 2003).  The server sits behind the new 2Wire
router that was installed when my client switched to U-Verse for "speed".  Granted, they have
all the speed they ever desired but there is no outgoing email.  NOTE:  Everything worked flawlessly
for the better part of 3 years with the ATT Netopia router.

Here is the current configuration:

- SBS Server with dual-NIC
- Internal network is using SBS DHCP with private 192.168.X.X range (all internal communication is working)
- External NIC is configured with a static IP that was purchased as part of a pool for this business.
- SBS machine is the only device connected to the 2Wire
- 2Wire internal gateway is set to the assigned static IP that was provided by ATT as part of the pool of (5)
- Subnet masks are set properly
- External IP of the 2Wire is a 108.X.X.X address (FYI)

All email and remote services are working as anticipated.  Firewall is using pinholes for hosted services.
NO EMAIL WILL LEAVE THE SERVER...

I am thoroughly exhausted at this point and I have pursued many avenues to troubleshoot this issue.  Instead of re-hashing everything I have tried, I encourage all of you to
request the information you feel would be most pertinent and I will be happy to provide it ASAP.

Thanks,
Sean
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MegaNuk3
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Is the server set to send email via DNS or smarthost? Check the server & Internet SMTP connector to see if the DNS servers it is using are working.
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seangarcia

ASKER

Originally it was using DNS for all outgoing mail and everything was working great with the Netopia router (different DNS servers than U-verse).  Since installing u-verse, we have tried the same configuration as before with new DNS servers, but no outgoing email.  We were getting a delay notification and the mail was sitting in outbound SMTP Connector queues for each domain represented.

Last night I tried to configure smtp.att.yahoo.com as a smarthost and using port 465 and 587 respectively, but neither worked.  Now all mail is sitting in one outbound SMTP Connector queue for smtp.att.yahoo.com.

The NDR is as follows:

There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.   <randrcpa.com #5.5.0 smtp;553 From address not verified - see http://help.yahoo.com/l/us/yahoo/mail/original/manage/sendfrom-07.html>

Can the Exchange server see the Internet? If you open a command prompt can you ping www.yahoo.fr ?
Yes, I can ping.  I have FULL FUNCTIONALITY of outgoing and incoming traffic with the exception of outgoing SMTP mail.  Internet connectivity is blazing with the new u-verse setup.  Internal traffic to server is working and internal email is working.

I have put the exchange server settings back to what they were pre-uverse:
- Use DNS to route email (not smarthost)

Now I do not get any NDR as stated above, but the message is just sitting int he outbound queue.  After some time, I will get a "delay notification" from Exchange.  The message will sit.  Then after a few days, I will get a NDR stating that the message sat for too long and was removed from the queue.

I have been on the phone with ATT U-Verse support (I think I am about to embark on a conversation with what I affectionately call  "Tier 5" support --- you can't write this stuff).
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seangarcia

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Thanks for the update. Glad you got it sorted.
There are other solutions to this issue that would allow you to work around AT&T's block on SMTP port 25, but I have opted for this solution simply due to the fact that there is no one at AT&T that can answer questions regarding the recommended way to deal with this issue.